Diisopropylethylamine → 2-[4-(dimethylamino)phenyl]-N-{[3'-(1-piperazinylmethyl)-3-biphenylyl]methyl}acetamide

HRID 2080328Notes

Reaction equation

HRID 2080328 reaction equation
C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[N:34]1([CH2:40][C:41]2[CH:42]=[C:43]([C:47]3[CH:52]=[CH:51][CH:50]=[C:49]([CH2:53][NH2:54])[CH:48]=3)[CH:44]=[CH:45][CH:46]=2)[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1.CCN(C(C)C)C(C)C.[CH3:64][N:65]([CH3:76])[C:66]1[CH:71]=[CH:70][C:69]([CH2:72][C:73](O)=[O:74])=[CH:68][CH:67]=1>C(Cl)(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:76][N:65]([CH3:64])[C:66]1[CH:71]=[CH:70][C:69]([CH2:72][C:73]([NH:54][CH2:53][C:49]2[CH:48]=[C:47]([C:43]3[CH:44]=[CH:45][CH:46]=[C:41]([CH2:40][N:34]4[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]4)[CH:42]=3)[CH:52]=[CH:51][CH:50]=2)=[O:74])=[CH:68][CH:67]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 1522034-N,N-dimethylaminophenylacetic acidHCID 2724699PyBOPHCID 67101934HCID 67101934, compound

Product 1

HCID 577367012-[4-(dimethylamino)phenyl]-N-{[3'-(1-piperazinylmethyl)-3-biphenylyl]methyl}acetamideYield 47.1%

Reagents, catalysts & solvents 1

HCID 19978452Chloroform trifluoroacetic acidSolvent

Procedure

A mixture of PyBOP (0.08 mmol in 200 mL of DMF), {[3′-(1-piperazinylmethyl)-3-biphenylyl]methyl}amine (44 mmol in 200 mL of DMF) and DIPEA (30 mL) were added to [4-(dimethylamino)phenyl]acetic acid (0.07 mmol). The resulting mixture was stirred for 16 hours at room temperature, then the solvent was removed under vacuum. The residue was dissolved in methanol and purified by loading onto a SPE cartridge (SCX, 500 mg), washing with MeOH, and eluting with a 2 M solution of NH3 in MeOH. The NH3 fraction was collected and evaporated under vacuum to give a gum which was dissolved in 1:1 CHCl3/TFA (0.5 mL). After stirring for 2 hours, the solvent was removed under vacuum and the residue was dissolved in MeOH. The free base of the compound was obtained by loading the solution onto a SPE cartridge (SCX, 500 mg), washing with MeOH, and eluting with 2M NH3/MeOH. The ammonia fraction was collected and the solvent was removed under vacuum to give the title compound (14.6 mg). LC/MS: m/z, 443 (M+H), 2.21 min.

Workup

  1. customthe solvent was removed under vacuum
  2. dissolutionThe residue was dissolved in methanol
  3. custompurified
  4. washwashing with MeOH
  5. washeluting with a 2 M solution of NH3 in MeOH
  6. customThe NH3 fraction was collected
  7. customevaporated under vacuum
  8. customto give a gum which
  9. stirringAfter stirring for 2 hours
  10. customthe solvent was removed under vacuum
  11. dissolutionthe residue was dissolved in MeOH
  12. customThe free base of the compound was obtained
  13. washwashing with MeOH
  14. washeluting with 2M NH3/MeOH
  15. customThe ammonia fraction was collected
  16. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-439de902695e460cb1ff45af2cd76549
Source dataset
uspto-grants-2011_04
Patent number
US07932247B2

Reaction notes

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